As the 1950s drew to a close, Claes Oldenburg—now renowned as the maker of monumental-but-whimsical public sculptures all over the world—arrived at a crossroads.

“I had trained as a painter,” recalls Oldenburg, seated in his huge SoHo studio and home. “The painting I was doing was very conservative. But there were new directions in the air, and people were fed up with Abstract Expressionism. I had to make this decision about how to present myself.”

Oldenburg was working on the then-gritty Lower East Side, and decided to take inspiration from what he saw every day. “That is what it’s all about—the work is made out of the materials of the place, the feeling of the place, and the look of the place,” says Oldenburg. “It takes its life from the surroundings.”

So, he zagged instead of zigged, eschewing traditional media for making installations, and in the early 1960s quickly created several still-influential bodies of work that are being celebrated in a multi-part exhibition at the Museum of Modern Art beginning next week: “Claes Oldenburg: The Street and The Store” and “Claes Oldenburg: Mouse Museum/Ray Gun Wing.”

For The Street, he literally represented what he saw while looking down, using cast-off materials like newspaper and burlap; eventually he dressed up like a bum and made himself part of the work in a gallery show. Mouse Museum and Ray Gun Wing are both clever collections of objects, some made by Oldenburg and some found, that are united by shape.

The Store may have the most lasting impact of all. “I started to make objects—things I could see in stores,” says Oldenburg of the witty, painted sculptures of cigarettes, ice cream sundaes, and hamburgers. “It seemed to me very logical to have a store of my own. What’s an art gallery but a store?” He rented a storefront, working in the back and showing his wares in the front—and quickly sold them to Met curator Henry Geldzahler, legendary dealer Ileana Sonnabend, and Andy Warhol.

“Once he decides, the next three years have him on a roll of unfathomable audacity and productivity,” says Ann Temkin, MoMA’s chief curator of painting and sculpture and the organizer of the shows.

The subtlety of Oldenburg’s work—which treads a fine line between satire and earnestness—is among the reasons Temkin thinks it feels so relevant to the art scene today. “It also has tremendous echoes in the work that young artists are making, given the penchant for materials that look junky and non-heroic, and the fascination with performance,” she says.

Plus, Oldenburg’s sense of humor makes it just plain fun. “I’m bringing my fourth-grader’s class,” adds Temkin. “I mean how many times in their life can they go to a big museum show that has sculptures of hamburgers and ice cream cones?”

“Claes Oldenburg: The Street and The Store” and “Claes Oldenburg: Mouse Museum/Ray Gun Wing” open at the Museum of Modern Art on April 14 and will be on view through August 5; moma.org